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wantstostroke Novice Jackinchatter

35 posts since 2015-08-16
42 year old heterosexual from twin cities area
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I recently became single so I rented a hotel room last night to have a fun cialis fueled night of stroking. While I was stroking I was drinking some beer and figured, "What the hell I'm buzzed...let's see if I can stroke with someone." So I figured I would put an ad up on Craigslist. About an hour later a guy messaged me back and we started to chat and exchanged pics. He said he would be up for an encounter in the morning. I replied that if I was awake I would be up for it.

I was hoping for that night but after one too many beers I just said "F this" and went to bed without getting to bust a load. Early in the morning he messaged me and said he was on his way. Well I couldn't sleep (never really can in new places) so I told him to come on up.

I had a quick beer to calm my nerves since I was nervous as hell since I had never done this before. He was also very nervous. We met in the lobby and went back to my room and turned on some big tits and cumshot porn.

We laid on seperate beds and we were enjoying what we were watching and he started rubbing his cock through his jeans. Then I started to rub my cock through my boxers. We keep rubbing our own cocks and then I see him take his out and start slowly stroking. So I take mine out and start doing the same.

As I am stroking he asks if he can lay by me in the bed I was in. I said sure and he laid next to me while we both had our cocks out. I was a little uncomfortable at first but the feeling eased the more I stroked.

He saw my bottle of lube and the fleshlights I brought (an Ice and a clear quick shot). He asked if I could pass the lube and I did. He then lubed up his cock and kept stroking. As he was stroking he glanced at my cocktail and asked if I minded. I wasn't planning on what was going to happen next but since I was hard as hell I figured "why not" and I took my hand off my cock. He then grabbed my cock and started stroking me. It felt different since I was only used to either myself or a lady stroking my cock. It was great though to be stroked while watching some cumshot compilations.

He stroked me for a minute and then I grabbed his cock and we started stroking each other. Remind you that I have never done anything like this before so it was completely out of character for me. We stroked each other for a few minutes and then I lubed up the quickshot and slid it on his cock. After a few strokes he repositioned himself and he started to suck my cock. That was very odd since it felt weird to have stubble rub up and down on my cock. It did feel good so I just let him for a while. He even sucked my cock while jacking me with the quickshot.

He laid down again and we started stroking ourselves for a bit. Then out comes the full sized fleshlight. He starts stroking with it then I start stroking with it. I then slipped the quickshot on him and we start jacking each other with the fleshlights. He said he was close to cumming and I took the full sizer and put it on his cock while he had the quickshot on and he came.

He cleaned up and offered to rinse out the fleshlight. I told him if he wanted to he could. So I am still laying in bed and then he takes the same fleshlight he came in and started stroking me with it. That was pretty hot. So he stroked me with it for a little bit and then I removed it and started stroking myself.

I started jacking fast since I wanted to cum. Once I started getting g close I grabbed the fleshlight that already had cum in it and came hard in it.

Then I cleaned up and he left and I hopped in the shower.

All in all it was a fun experience. May have to try that again but without the oral.
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palmfull69 Novice Jackinchatter

43 posts since 2016-03-20
66 year old heterosexual from Earthling
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Sounds fun
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batebudforu Amateur Jackinchatter

261 posts since 2016-01-19
38 year old curious male from Missoula, MT
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I would love to have a night like that with anyone... I am fantasizing about that right now and really wish I had your fleshlight wrapped around my cock...my cock is throbbing with precum thinking about it
Skype Batebudforu
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angelito1978 Amateur Jackinchatter

307 posts since 2013-06-06
46 year old curious
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Hot story... sounds risky
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Sounds like a good time. Never done anything like that yet.
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freewank Novice Jackinchatter

4 posts since 2013-11-13
32 year old curious male from Yorkshire, England
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This sounds so much fun, kind of how I'd like things to go for me sometime. Same feels about the oral though, not sure I would like it. Everything else though, yes please!
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iBalls Skilled Jackinchatter

673 posts since 2010-08-29
54 year old curious from Ottawa, Ontario
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Dude, you MUST do this next time: double-fuck one of your Fleshlights from either end. First time I did this, we both came (for the first time) within 60 seconds. Feeling another cock fucking alongside yours in a tight, wet pussy--or pussy proxy--is out of this world. I came when I felt his cock jump and jerk and then his warm sperm envelop my dick inside the FL.
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TATTOOWHITETRASH Novice Jackinchatter

13 posts since 2014-08-27
49 year old curious from Dallas
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You are not kidding. Years ago me and my roommate were double teaming this girl taking turns fucking her doggy style while she blew the other when she got on top of me and was riding me my roommate came up behind her and put his dick inside her too. I about came the instant he did. feeling his cock rubbing against mine inside her was amazing
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baterMike69 Skilled Jackinchatter

556 posts since 2015-01-01
51 year old curious male from South Jersey
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Sweet! It only gets better. CL is great for rounding up horny guys. I use it only when I travel never near home. I usually get two or three guys pelting. I always tell me to bring an UNopendd bottle of scotch, or bourbon. We have a few shots, watch porn on the laptop and enjoy our dicks. Some touch, some get touched, we all cum. ain't it great?
I do love getting jackMail so turn me on....
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wantstostroke Novice Jackinchatter

35 posts since 2015-08-16
42 year old heterosexual from twin cities area
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It was a fun time. Wouldn't mind doing it again lol. May have to try double fucking my fleshlight sometime. That does sound fun! Next time though I do want to find a dude who has some time so we can cum more than once
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Sounds a little scary, but a LOT fun!!!
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ozjacker Skilled Jackinchatter

518 posts since 2012-12-29
61 year old
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first time is always memorable grin
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